Beta-lactamase inhibitor prodrug

A prodrug having the structure:

• 39
• and solvates thereof.

A pharmaceutical composition comprising:

• (a) 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-(hydroxymethyl)-3,3-dimethyl-7-oxo-, (1R)-1-(benzoyloxy)ethyl ester, 4,4-dioxide (2S, 5R, 6R), or a solvate thereof,
• (b) amoxicillin, and
• (c) a pharmaceutically acceptable excipient.

A method for increasing the therapeutic effectiveness of a beta-lactam antibiotic in a mammal comprising administering to said mammal an effective amount of a beta-lactam antibiotic and an effectiveness-increasing amount of a prodrug having the structure:

• 41
• wherein R is H or methyl, or a solvate thereof.

A method of treating a bacterial infection in a mammal by administering to said mammal an effective amount of a beta-lactam antibiotic and an effectiveness-increasing amount of a prodrug of having the structure:

• 42
• wherein R is H or methyl, or a solvate thereof.

A method of treating a bacterial infection in a mammal by administering, to a mammal in need thereof, a therapeutically effective amount of a pharmaceutical composition comprising:

• (a) 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-(hydroxymethyl)-3,3-dimethyl-7-oxo-, (1R)-1-(benzoyloxy)ethyl ester, 4,4-dioxide (2S, 5R, 6R), or a solvate thereof;
• and
• (b) a pharmaceutically acceptable excipient.

A method of treating a bacterial infection in a mammal by administering, to a mammal in need thereof, a therapeutically effective amount of a pharmaceutical composition comprising:

• (a) 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-(hydroxymethyl)-3,3-dimethyl-7-oxo-, (1R)-1-(benzoyloxy)ethyl ester, 4,4-dioxide (2S, 5R, 6R), or a solvate thereof,
• (b) amoxicillin, and
• (c) a pharmaceutically acceptable excipient.